Reaction #1121733

Reaction equation

water

3-(dimethylamino)-1,2-propanediol

imidazole

tert-butyldimethylsilyl chloride

→

1-(tert-butyldimethylsilyloxy)-3-(dimethylamino)propan-2-ol

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   OtherThe organic layer was separated
2. 2
   Extractionthe aqueous layer was extracted with two additional portions of dichloromethane (20 mL)
3. 3
   DryingThe combined organic extracts were dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Procedure

A dry dichloromethane (10 mL) solution of 3-(dimethylamino)-1,2-propanediol (98%, 1.00 g, 8.39 mmol, 1.0 equiv) and imidazole (0.57 g, 8.39 mmol, 1.0 equiv) was stirred at 0° C. under argon for 15 minutes. Solid tert-butyldimethylsilyl chloride (1.26 g, 8.39 mmol, 1.0 equiv) was added to the mixture and the resultant was stirred for 2 hours at 0° C. The mixture was then diluted with 20 mL of dichloromethane and poured into deionized water (15 mL). The organic layer was separated and the aqueous layer was extracted with two additional portions of dichloromethane (20 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to afford crude 1-(tert-butyldimethylsilyloxy)-3-(dimethylamino)propan-2-ol, a thick clear oil, which was used without further purification.

Source